Diisopropylamine → HCID 68831356, compound
Reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][CH2:14][O:15][C:16]([CH3:18])=[O:17].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]=[CH:34][N+:35]([O-:37])=[O:36])[CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:14]([O:15][C:16](=[O:17])[CH2:18][CH:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:28]=1)[CH2:34][N+:35]([O-:37])=[O:36])[CH3:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a dry round bottom flask was added 2.7 mL of diisopropylamine and 20 mL THF. The mixture was cooled to −78° C. with stirring. A solution of n-BuLi (11.4 mL, 1.6 M) was added dropwise and the resulting solution was stirred for 20 min. EtOAc (1.5 mL) was added slowly to quench and the mixture was stirred for an additional 20 min. 1-Benzyloxy-3-(2-nitrovinyl)benzene (3.4 g, 13 mmol) in 50 mL THF was then added and the solution was stirred for 2 h. The mixture was warmed to r.t., quenched with sat. NH4Cl solution (50 mL), extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 3.2 g of the desired product.
Workup
- stirringthe resulting solution was stirred for 20 min
- customto quench
- stirringthe mixture was stirred for an additional 20 min
- stirringthe solution was stirred for 2 h
- temperatureThe mixture was warmed to r.t.
- customquenched with sat. NH4Cl solution (50 mL)
- extractionextracted with EtOAc
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-b3e077c71f0e4590bfb034c267e652ef
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601742B2
Reaction notes
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